51294-75-8

Usage

InChI:InChI=1/C11H11BrN2/c1-8-11(12)9(2)14(13-8)10-6-4-3-5-7-10/h3-7H,1-2H3

Upstream product

• 1131-16-4 3,5-dimethyl-1-phenyl-1H-pyrazole 
• 123-54-6 acetylacetone 
• 59-88-1 phenylhydrazine hydrochloride 
• 22042-79-1 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde 

Downstream Products

• 20638-31-7 4-bromo-1-phenyl-1H-pyrazole-3,5-dicarboxylic acid 
• 143032-06-8 Benzenesulfonyl-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-acetonitrile 
• 1157-37-5 (3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)phenylmethanone 
• 387353-96-0 3,5-dimethyl-4-dimethylphenylsilyl-1-phenylpyrazole 
• 1213264-57-3 3,5-dimethyl-4-mesityl-1-phenyl-1H-pyrazole 
• 1213264-58-4 4-(2,6-dimethylphenyl)-3,5-dimethyl-1-phenyl-1H-pyrazole 
• 1387506-52-6 4-bromo-2,3,5-trimethyl-1-phenyl-1H-pyrazol-2-ium tetrafluoroborate 
• 1387506-41-3 4-bromo-2-ethyl-3,5-dimethyl-1-phenyl-1H-pyrazol-2-ium iodide 
• 1131-16-4 3,5-dimethyl-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond

A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

A mild halogenation of pyrazoles using sodium halide salts and Oxone

A mild, inexpensive, and operationally simple pyrazole halogenation method utilizing Oxone and sodium halide salts is reported. This work documents 17 examples of alkyl, aryl, allyl, and benzyl substituted 4-chloro and 4-bromopyrazoles, obtained in up to 93% yield. Reactions are performed in water under ambient conditions and generation of organic byproducts is avoided.

Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles

The relative ligand donor strengths of 10 pyrazole-derived ligands has been determined with great accuracy, making use of the interdependence between the donor strength of the co-ligand and the 13C NMR chemical shift of the iPr2-bimy carbene signal in trans-[PdBr2( iPr2-bimy)L] complexes (iPr2-bimy = 1,3-diisopropylbenzimidazolin-2-ylidene; L = pyrazole-derived ligand). Even subtle variations in the substitution pattern of the pyrazole backbone up to three bonds away from the coordinating nitrogen could be detected reliably using this methodology. Alkylation experiments conducted on the pyrazoles using electrophiles of varied reactivity (ethyl bromide, ethyl iodide, and trimethyloxonium tetrafluoroborate) served as a benchmark to rank the pyrazoles in three groups of gradually increasing nucleophilicity, which correlated well with their determined donor strength.

Reactions of 3,5-dimethyl-1-phenyl-1h-pyrazole with electrophiles

Reactions of 3,5-dimethyl-1-phenyl-1H-pyrazole with various electrophilic reagents were studied. Electrophilic attack occurred regioselectively at the C4 atom in the pyrazole ring. Pleiades Publishing, Ltd., 2012.

Nitrogen-containing heterocycles from metal β-diketonates

Factors determining the reaction of metal β-diketonates with hydrazine, in particular the nature of central metal ion and structure of β-diketonate ligand, are discussed. The possibility for the preparation of other heterocyclic compounds via reaction of metal acetylacetonates with phenylhydrazine, o-phenylenediamine, urea, and thiourea was studied.

Halogenation of pyrazoles using N-halosuccinimides in CCl4 and in water

Reaction of pyrazoles with N-halosuccinimides (NXS, X=Br, Cl) in either CCl4 or water gave 4-halopyrazoles in excellent yields. The reaction was carried out under mild conditions and did not require any catalysts or special precautions. The reaction provides an efficient method for 4-C halogenation of pyrazoles. Copyright Taylor & Francis Group, LLC.

A mild and efficient method for halogenation of 3,5-dimethyl pyrazoles by ultrasound irradiation using N-halosuccinimides

The 4-halo-3,5-dimethyl pyrazoles have been synthetisized in good yields in short reaction times in the absence of a catalyst by reaction of 3,5-dimethyl pyrazoles with N-halosuccinimides (NBS, NCS and NIS) under ultrasound irradiation. Finally, the halogenation of pyrazoles with Br2, IC1 and I2 was showed in similar conditions.

Palladium-catalyzed cross-coupling reaction of haloazoles with phenylsulfonylacetonitrile

Condensation of halo-substituted 1,3-azoles (1,3-oxazoles, 1,3-thiazoles and imidazoles) with phenylsulfonylacetonitrile under basic conditions was promoted by catalytic action of tetrakis(triphenylphosphine)palladium(0) to give α-phenylsulfonyl-1,3-azole